A Day Trip to Rockport, MA

If you have a trip to Boston planned (or even if you live in the city) and are looking to spend some time soaking up some of that quintessential New England charm, Rockport is a great choice. Though there are plenty of things to do in Rockport, if you’re short on time, you can still get a great feel for the place in a day or less. One super convenient part about visiting Rockport is that it’ll only take you about an hour regardless of whether you drive or take the train. I’m a big fan of the train because aside from needing to keep on top of the timetable, I can do other things while en route. 

Before you go + getting there

If you’re driving:

Because it’s such a small town, you’ll need to make sure that you’re at least peripherally aware of the parking situation. We went on a Sunday in high season and parking wasn’t terribly difficult. It also seemed that visitor parking was allowed throughout the downtown area. We parked about a 4 minute walk from the center of the action, directly in front of someone’s house. But in the interest of being safe I would check Rockport’s parking website.

If you’re taking the train:

You’ll pick up a commuter rail train at North Station and will pass a few other notable towns that you might want to hop off the train to check out. The Rockport MBTA station is about a 15-minute walk from the main tourist area.

(If you’re reading this in the summer of 2018 the MBTA is running a special program where you can get a $10 round-trip ticket for Weekends use only on all commuter lines through September 2nd. For more information check out the website.)

When to go to Rockport:

Rockport is most busy in the height of the summer, but it’s a lovely place to visit year-round. A trip during the fall or the spring may be best for you if you’re looking to avoid the large crowds. Because it’s so small, and is so close to Boston, a day trip up even during peak visitor season is still lovely.

Things to do in Rockport

Get a lobster roll.

There are a handful of restaurants in Rockport, so you’ll certainly not starve. Getting a lobster roll is a very New England thing to do – and it’s what I did! Being from the area, I’ve had a fair share of  lobster rolls and this one from the Blue Lobster Grille stacked up ok (my #1 favorite is on Cape Cod and virtually untouchable – maybe I’ll do a write up on that sometime soon). I will say though… I’ll always opt for chips over fries, but the fries that came with this particular sandwich…. were unreal they were so good!

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Check out motif number one.

You want me to go where? I knew the image and I had heard of Motif Number 1, but when you hear an artsy name like that, one generally thinks of a painting. In this particular case you would be 1/2 right. Motif Number 1 is an exact replica of an old fishing shack that was built in 1840 and destroyed in 1978 (in a blizzard), and was widely considered the most often painted building in America.

Go to the beach.

There are a couple different beaches that are pretty close to the main area in Rockport. They’re not the largest beaches, but they looked like a lot of fun (we spotted a few fun floating toys – including a massive inflatable duck)

Take a walk on the jetty.

There is a long jetty that sticks out at the end of the main shopping area. If you’re looking to get a good photo angle or tire out some kids, definitely go all the way to the end.

(For some more info about visiting Rockport, check out this post by my fellow New Englanders over at Two Drifters! Big thanks to them for letting me use the photo above!)

Shop for seaside trinkets.

There are loads of little shops in the area if you need to grab a souvenir (or forgot something at home – like sun screen or sun glasses). A good handful of the shops have local crafts, too.

Kayak!

You can rent a kayak to explore the harbor a little more.

Grab some ice cream.

There was no shortage of ice cream in Rockport! In the span of maybe 5 minutes we walked past probably 3 or 4 different places. There are also other clod or sweet treat options along the way. I almost got an iced coffee, but knowing that ice cream was going to be in my near future, I figured two stimulants might be a bad idea given my personal baseline is already a little intense.

Wander the residential neighborhoods.

Closer to the water, it appeared that most of the houses were rentals, but up by where we parked felt a lot more like the local residences. The houses were beautifully combination of  the weathered look and bold colors.

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Pet all the dogs.

Holy cow were there a lot of dogs wandering around. Any by “wandering around” I mean leashed and very well-behaved accompanied by their owners. We spotted a bulldog, a pair of twinning golden retrievers, a very small…. something? The point is that there are lots of dogs and you should (ask to)) pet them. 

Make friends with someone who has a boat.

Lots of boats in the harbor and wouldn’t it be great to be able to go out on the water for just a few minutes? Or you can find a boat tour that suits you – Cape Ann Harbor Tours has a few options!


Rockport is a lowkey destination with a lot of charm. It’s less a place where you visit and plan to have a packed itinerary, and more a place to enjoy summer the New England way.

If you’re not convinced that you’ll have enough to do (I know I love to jam-pack my itineraries), one great idea is to take the earliest train up to Rockport and enjoy the morning by grabbing breakfast and wandering around before the crowds roll in. Once you’ve had your fill, hop back on the inbound train and go one stop to Gloucester. Hop off and wander around another coastal town (with a slightly different feel). Stick around there for another meal and when you’re ready, grab another inbound train. Get off at the stop for Salem and you’ll have a bit of time to look around and grab something to drink at one of the many bars, or my favorite cider tasting room – Far From the Tree (if you know me in real life, you already know I’m a super-fan). When you’ve had your fill, take the train back into the city.


  • What are some markers of summer where you’re from? Maybe it’s a specific food or a festival – tell me below!
  • Have you visited New England? What are your favorite places in the area?
  • What do you think about lobster: the best thing ever or highly overrated?
Posted in Boston, City Guides, Inspiration, New England, Travel, Trip Planning, USA.

16 Comments

  1. We all need more friends who own boats! I’ve never tasted a lobster roll before, and I should because the whole concept confuses me a little. I can’t imagine how the texture of bread goes with lobster. But then I haven’t actually eaten lobster before either. Obviously, I need a trip to Rockport stat.

    • I resisted it for a looong time and then someone convinced me to try a bite of theirs and I loved it. Now even though I don’t really eat meat/fish, I’ll usually have 1 or 2 lobster rolls during the season just for nostalgia’s sake

  2. I have never heard of Rockport but it looks like a great little town. You had me sold with that lobster roll! It looks so delicious. I hope to visit Boston during the fall so would definitely consider visiting Rockport! Thanks for sharing 🙂

    • Ohh yeah Boston in the fall is really nice! Just keep an eye on the hotel/hostel rates in October – there are a few big conventions that drive up prices in the city during certain weeks.

  3. We are from Nova Scotia and everything you described about Rockport sounds like where we are from – the world is so big but so small at the same time. Lobster is amazing, hubby doesn’t think so – we are in different camps on that one! We have been to Salem a few times, my Dad goes to Gloucester annually and rows in a dory race there. We have yet to go to Rockport but we are in New England quite a bit so maybe one day – I want to pet ALL THE DOGS after all!! 🙂

  4. Love..love lobster rolls!! So delicious, yummy shot!! It’s been years since I visited Boston, though I heard about Rockport. What a quaint town. Will certainly check it out the next time we’re in the area.

  5. Ooh, I’m so glad I found this. Not only do I adore lobster rolls, but I will be visiting Boston next spring. I have heard of Rockport but didn’t know that much about it, but it looks really cute and worth a look. Thanks for posting.

  6. Rockport looks so darling! I’ve really only been to Boston, but now you have me wishing I had made this day trip. I love your tips of petting all the dogs and befriending a boat-owner. If I couldn’t manage to do that, I’d definitely take one of the tour. I’d definitely treat myself to a sweet treat from one of the ice-cream shops as well.

  7. I loved visiting so much we moved here! My kids are growing up in this idylic town, independent and sitter free by middle school, organizing their own whffle ball games or candy store raids. Businesses hire them seasonally, giving them skills, work ethic and financial independence in high school. And my kids have thrived at the schools, now taking my oldest to her first year of college in DC. It helps if you can telework a couple of days a week, worth the commute to live in new england family paradise

  8. Just went to Rockport on Wednesday. Love the town. Next time try Helmut’s Strudel Shop and sit on the deck in back of the shop. Nothing better than an ocean breeze, warm strudel and iced coffee on a Summer afternoon.

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